Yeah you need someone getting into the box to get on the end of those crosses.
I have almost the same setup except my striker is a CF(s) and my left IF has an attacking duty, making him act like a second striker at times. I score plenty of goals from crosses from the right winger.
This is my setup:
Standard mentality, Structured team shape, TIs: Close down more, Retain possession, Play out of defense.
When playing at home or big favorites away I usually change to Control.

Well yeah, as long as we win it of course . I don't know if I can deal with another world cup final defeat...
Actually my ideal scenario would be semis against Argentina and winning the final against Germany. All our world cup traumas will be dealt with!

Counter IS quick ... but only when you are countering.
So you will play a slow, patient game, not taking too many risks, waiting for your opponent to make a mistake... then when the counter is "on" the team suddenly bursts forward and the tempo is very quick, until the counter ends.

This is a great thread, thanks.
One thing that I've been wondering about - you have Hassle Opponents set as a team instruction. Now (as far as I know) what this does is set Closing Down instructions to maximum for the whole team. Wouldn't this nullify any individual closing down instructions you set for players? So tailoring pressing as you say won't work if you have Hassle Opponents set.
Personally I'm fiddling around with my own high pressing tactic, and I've moved away from Hassle Opponents. My central defenders get pulled out of position too much for my liking. What I do now is leave my defensive trio (DC,DC,DM) as is and set Close Down More for all the other players.

It really depends on which club they get loaned out to and if they get a lot of playing time. The club should have good training facilities and the league that the loanee will play in should be good enough to provide a decent learning experience.
However, I personally like to keep the really talented youngsters (that I definitely plan on keeping) at the club. This has several advantages:
- After 3 years at your club they become homegrown
- I can give them first team appearances, which is the best way to raise their ability.
- By staying at the club and country they have an easier time settling in, learning the language if they are foreign, developing good relationships with the backroom staff and other players, etc.
So at the end of the day I only loan players out that I plan on selling anyway. It's a good way to raise their value and develop them a bit so you can cash in on them later.

I like to use "drop deeper", "play wider", "pass into space". Draw them out and stretch them out. If they're giving you a lot of time on the ball (not closing down) then you can also use "run at defense".